Bertolini Mark T 4
4 · Oscar Health, Inc. · Filed Jul 1, 2026
Research Summary
AI-generated summary of this filing
Oscar Health CEO Mark T. Bertolini Sells $35.8M in Shares
What Happened
Mark T. Bertolini, CEO of Oscar Health (OSCR), sold a total of 1,238,996 shares in open-market transactions on June 29–30, 2026, generating total proceeds of about $35.77 million. The individual transactions reported were:
- 555,826 shares at $29.17 — $16,213,444 (6/29)
- 58,926 shares at $30.08 — $1,772,494 (6/29)
- 488,654 shares at $28.35 — $13,853,341 (6/30)
- 135,590 shares at $28.97 — $3,928,042 (6/30)
These sales were reported as dispositions (S). Such sales are commonly routine (e.g., to cover taxes) rather than a buy signal.
Key Details
- Transaction dates: June 29, 2026 and June 30, 2026; Form 4 filed July 1, 2026 (appears timely).
- Total shares sold: 1,238,996; total proceeds: ~$35.77M.
- Post-transaction holdings: Not specified in the excerpt provided — see the full Form 4 for total beneficial ownership after these sales.
- Footnotes: Sales were effected to satisfy tax withholding related to deferred settlement of performance stock units that vested April 3, 2026, pursuant to a Rule 10b5-1 instruction letter entered 11/10/2025 and amended 3/24/2026. Reported prices are weighted averages; the underlying trades were executed across price ranges (roughly $27.78–$30.61 per share) as detailed in the filing. The reporting person will provide a price-by-price breakdown on request.
Context
These transactions were sales to cover tax obligations tied to vested equity (not new purchases). For retail investors, purchases or insider-initiated acquisitions often carry more interpretive weight than routine sales for tax or settlement reasons. The filing identifies a 10b5-1 plan, which indicates pre-scheduled execution rather than opportunistic trading.
Insider Transaction Report
Form 4
Bertolini Mark T
DirectorChief Executive Officer
Transactions
- Sale
Class A Common Stock
[F1][F2][F3]2026-06-29$29.17/sh−555,826$16,213,444→ 8,434,740 total - Sale
Class A Common Stock
[F1][F4][F3]2026-06-29$30.08/sh−58,926$1,772,494→ 8,375,814 total - Sale
Class A Common Stock
[F1][F5][F3]2026-06-30$28.35/sh−488,654$13,853,341→ 7,887,160 total - Sale
Class A Common Stock
[F1][F6][F3]2026-06-30$28.97/sh−135,590$3,928,042→ 7,751,570 total
Footnotes (6)
- [F1]Represents sale of shares to satisfy tax withholding obligations in connection with the deferred settlement of performance stock units that vested on April 3, 2026. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on November 10, 2025 and amended and restated on March 24, 2026.
- [F2]The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.74 to $29.73, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.
- [F3]Includes shares to be issued in connection with the vesting of one or more restricted stock units.
- [F4]The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.74 to $30.61, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.
- [F5]The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $27.78 to $28.77, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.
- [F6]The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.78 to $29.29, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.
Signature
/s/ Melissa Curtin, Attorney-in-Fact|2026-07-01